WO1997039726A1 - Diacide oxa et composes voisins pour traiter les problemes de peau - Google Patents

Diacide oxa et composes voisins pour traiter les problemes de peau Download PDF

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Publication number
WO1997039726A1
WO1997039726A1 PCT/US1997/006973 US9706973W WO9739726A1 WO 1997039726 A1 WO1997039726 A1 WO 1997039726A1 US 9706973 W US9706973 W US 9706973W WO 9739726 A1 WO9739726 A1 WO 9739726A1
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Prior art keywords
acid
composition
compound
skin
group
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PCT/US1997/006973
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English (en)
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Dmitri Ptchelintsev
Neil Scancarella
Robert Kalafsky
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Avon Products, Inc.
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Priority to JP53835597A priority Critical patent/JP3779733B2/ja
Priority to BR9708747-5A priority patent/BR9708747A/pt
Priority to EP97924518A priority patent/EP0910331B1/fr
Priority to CA2251746A priority patent/CA2251746C/fr
Priority to DE69730604T priority patent/DE69730604T2/de
Priority to AT97924518T priority patent/ATE275383T1/de
Publication of WO1997039726A1 publication Critical patent/WO1997039726A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to a new class of compounds for use as active principals for topical treatment of skin conditions, to compositions containing these compounds and to methods of treating skin conditions using these compounds and compositions
  • Compounds of the class include those of Formula (I) :
  • alpha hydroxyacids having an all carbon backbone is described in U.S. Patent No. 5,091,171.
  • Cosmetic compositions using 2- hydroxyalkenoic acid are disclosed, for example, in U.S. Patent No. 5,108,751.
  • Such compounds must have an unsubstituted alpha hydoxy group on a carbon backbone and are purportedly used to impart beneficial effects to the skin.
  • the trend is away from the use of such alpha hydroxyacids since they necessitate low operational pH ranges that for the most common forms, i.e. glycolic and lactic acids, are known to cause skin irritations.
  • Topical formulations comprising straight, all carbon backbone, dicarboxylic acids have been proposed as replacements for alpha hydroxyacids.
  • U.S. Patent Nos. 4,292,326, 4,386,104 and 5,385,943 describe the use of dicarboxylic acids having 7 to 13 carbon atoms for various skin indications.
  • U.S. Patent No. 4,885,282 states that a 4 to 18 carbon dicarboxylic acid compound is useful for the treatment of skin disorders.
  • dicarboxylic acids that have all carbon backbones are solid at ambient temperatures, extremely difficult to work with and, if a solution is achieved, the result is an aesthetically unpleasant mixture unsuitable for cosmetic use.
  • the basic compound of this invention is a compound of the following Formula (I) :
  • X, Xi, 2 r X 3 , Y and Z are independently, 0, NH, or S.
  • Preferred are those compounds in which X, X i f X 2/ X 3 , Y and Z are all oxygen.
  • Most preferred are those compounds in which X, Xi, X 2 , X 3 , Y and Z are each oxygen, and Ri, R 2 , R 3 , Rs, Re, T, Re, R9, Rio and R n/ are each hydrogen.
  • the preferred non-hydrogen substituents include alkyls alkenyls, oxa-alkyls, aralkyls and aryls.
  • non-hydrogen substituents include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, heptyl, octyl, nonyl, dodecanyl, ethoxy, ethoxy, propoxy, butoxy, cyclohexenyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, cyclobutyl and cyclohexanyl.
  • Exemplary compounds of Formula (I) include 3,6- dioxaoctadioic acid (HOOC-CH 2 -O-CH 2 -CH 2 -O-CH 2 -COOH) ;
  • Compounds of Formula I can also be prepared from commercially available polamines, polyols and polythiols by routine chemical reactions well known to those skilled in the art such as amidation, catalytic oxidation, esterification and other well known organic chemistry synthetic protocols, as described in organic chemistry textbooks including March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd ed., John Wiley Interscience (1985) and Carey et al. Advanced Organic Chemistry, 3rd ed.. Parts A and B, Plenum Press, New York (1990) .
  • oxa compounds useful in the topical compositions of this invention can also be in the form of derivatives that are converted back to an acidic form by action of hydrolytic enzymes in the skin such as glycosidases, phosphatases, esterases and amidases.
  • suitable derivatives include esters of Formula I compounds with aliphatic alcohols, carbohydrates, amides, lactones and anhydrides
  • oxa diacids and/or oxa compounds
  • oxa diacid compounds oxa diacid compounds
  • a “topical composition” refers to a composition intended to be directly layed onto or spread on the surface of skin.
  • An “effective amount” means an amount of a compound or a composition sufficient to induce a positive change (e.g. normalization of desquamation) in the skin condition to be treated such as those attributed to, accompanied or exacerbated by abnormal desquamation.
  • physiologically acceptable vehicle or a “suitable topical vehicle” refers to drugs, cosmetics, medicaments or inert ingredients that are suitable for use in direct contact with human tissues without undue toxicity. All percentages refer to weight percent, based on the total weight of the topical composition.
  • oxa compounds are used as active principals in topical applications to treat various skin conditions attributed to, accompanied by or exacerbated by abnormal desquamation, Such conditions include, but are not limited to, dry skin, ichthyosis, palmar and plantar hyperkeratoses, dandruff, lichen simplex chronicus, Dariers disease, keratoses, lentigines, age spots, melasmas, blemished skin, acne, psoriasis, eczema, pruritis, inflammatory dermatoses, striae distensae (i.e. stretch marks), warts and calluses.
  • dry skin ichthyosis, palmar and plantar hyperkeratoses, dandruff, lichen simplex chronicus, Dariers disease, keratoses, lentigines, age spots, melasmas, blemished skin, acne, psoriasis, eczema, pruritis,
  • the compounds are unexpectedly and surprisingly found to be useful as active agents in topical preparations for treating signs of dermatological aging, both photoaging and intrinsic aging, including skin wrinkles such as fine wrinkling in the eye area or "crows feet” or fine wrinkles around the mouth area, irregular pigmentation, sallowness, loss of skin resilience and elasticity.
  • Oxa compounds and topical compositions containing them are also useful for treating disorders associated with the nails, cuticles and hair such as ingrown hair, folliculitis and Pseudofolliculitis barbae.
  • the present compounds also soften hair and promote the elimination of hair ingrowths, making the compounds of Formula (I) useful in shaving compositions.
  • the oxa compounds can be incorporated into the compositions as free acids or as corresponding salts derived by neutralization with organic or inorganic bases such as triethanolamine, arginine, lysine.
  • organic or inorganic bases such as triethanolamine, arginine, lysine.
  • the effective amount of the oxa compound can be within the range from about 0.1% to about 95%. Both the effective amount and the frequency of application will vary depending on the particular skin condition treated, the age and physical condition of the person under treatment, the severity of the condition, the duration of treatment, the nature of concurrent treatments, the specific compound or compositions employed, the particular vehicle utilized to deliver the compound or compositions, and other like factors within the knowledge and expertise of those skilled in the art.
  • the efficacy of the oxa compounds in treating skin conditions has been found to be affected by the pH of the composition. It is believed desirable to maintain the pH of the composition in the acid range pH ⁇ 7.0, preferably pH ⁇ 5.0, most preferably in the pH range between 3.5 and 4.0.
  • the pH of the composition can be adjusted by adding water soluble salts formed by strong bases (e.g. KOH, NaOH, NHOH) and weak acids (e.g. phosphoric acid, acetic acid, lactic acid, carbonic acid) . Examples of such salts include potassium biphosphate, sodium phosphate, sodium acetate, sodium lactate and the like. Other methods useful for adjusting the pH of topical compositions are known to those skilled in the art.
  • compositions of the present invention have clear advantages over alpha hydroxyacid formulations, including superior mildness.
  • Formulations containing alpha hydroxyacids can cause substantial discomfort to some individuals and symptoms of severe skin irritation in others, upon facial application. For instance, a formulation containing 4.0% glycolic acid at pH 3.7 produced a skin irritation (PII) score of 0.23 when tested on 20 panelists.
  • a composition containing 10% of 3,6, trioxaundecanedioic acid at pH 3.7 produced a PII score of only 0.13 (see Example 2, below) .
  • compositions that manifest a PII score of less than or equal to 0.15 are considered non-irritating; those exhibiting PII scores between 0.15 and 0.3 are considered moderately irritating; and compositions that elicit a PII score of more than 3.0 from tested panelists are considered serious irritants.
  • the PII scoring takes into consideration such factors as the number of panelists displaying irritation symptoms compared to the total number of panelists in the test. While being significantly gentler to skin than glycolic acid formulations, the oxa diacid compositions of the present invention are highly effective in normalizing the desquamation of the upper stratum corneum, an activity required for the alleviation of the skin conditions listed above.
  • compositions of the present invention also have advantages over compositions containing dicarboxylic acids including better water solubility and superior stratum corneum desquamatory activity.
  • Oxa diacids easily dissolve in water to concentrations of at least 20 to 30% by weight and, therefore, allow a much wider range of composition flexibility.
  • Dicarboxylic acids of moderate to long chain length, which have straight, all-carbon backbones, are virtually insoluble in water and other aesthetically acceptable vehicle. This severely limits the choice of delivery vehicles for the dicarboxylic acids.
  • the desquamatory activity of such dicarboxylic acids is also questionable. For example, formulations containing 5% and 10% dodecanedioic acid do not produce any normalizing effect on stratum corneum desquamation beyond that of its vehicle alone.
  • vehicles found to be suitable for use with the oxa compounds include; (1) (a) about 2 wt% to about 10 wt% glycerin, (b) about 1 wt% to about 10 wt% propylene glycol, (c) about 0.1 wt% to about 2 wt% hydroxyethyl cellulose, (d) about 0.1 wt% to about 1 wt% imidazolidilyl urea, and (e) about 0.01 wt% to about 2 wt% disodium-EDTA;
  • the topical compositions of the present invention can be made as lotions.
  • a first or more basic lotion comprises about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacid, and the remainder water.
  • a second lotion has about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacid, about 0.5 to about 50% of an emollient about 0.1 to about 30% of an emulsifier and the remainder water.
  • the second lotion may also contain up to about 10% of a preservative, from about 0.1 to about 3% of a fragrance, and up to about 5% of a dye or a pigment.
  • the topical composition of the invention can also be formulated as a cream.
  • a first or more basic cream comprises about 0.1 to about 95%, preferably from about 1 to about 50%, and most preferably about 5 to about 20%_of the oxa diacid, from about 0.5 to about 50% of an emollient, about 0.1 to about 6% of a thickener and the remainder water.
  • a second, preferred cream comprises about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacid, from about 0.5 to about 50% of an emollient, about 0.1 to about 30% of an emulsifier, about 0.1 to about 6% of a thickener and the remainder water.
  • the oxa diacid can be combined with most conventional emollients including mineral oil, petrolatum, paraffin, ceresin, ozokerite, microcrystraline wax, perhydrosqualene dimethyl polysiloxanes, methylphenyl polysiloxanes, silicone- glycol copolymers, triglyceride esters, acetylated monoglycerides, ethoxylated glycerides, alkyl esters of fatty acids, fatty acids and alcohols, lanolin and lanolin derivatives, polyhydric alcohol esters, sterols, beeswax derivatives, polyhydric alcohols and polyethers, and amides of fatty acids.
  • suitable emollients can be found in Sagarin, Cosmetics, Science and Technology, 2nd Ed., vol. 1, pp. 32-43 (1972), the contents of which are incorporated herein by reference.
  • the emulsifiers that can be cationic, anionic, nonionic or amphoteric, or a combination thereof.
  • Nonionic emulsifiers are preferred.
  • Exemplary nonionic emulsifiers are commercially available sorbitans, alkoxylated fatty alcohols and alkyl polyglycosides.
  • Anionic emulsifiers may include soaps, alkyl sulfates, monoalkyl and dialkyl phosphates, alkyl sulphonates and acyl isothionates.
  • Other suitable emulsifiers can be found in McCutcheon, Detergents and Emulsifiers, North American Edition, pp. 317-324 (1986), the contents of which are incorporated herein by reference.
  • the preservatives suitable for use with the present compositions include alkanols, especially ethanol and benzyl alcohol, parabens, sorbates, urea derivatves, and isothiazolinones.
  • While such lotions or creams can be made using conventional homogenization methods known to those skilled in the art, it is also possible to use a process of microfluidization that involves co-mixing the aqueous phase and the oil phase of such creams and lotions in a high-pressure ho ogenizer that reduces the emulsion particle size dramatically to about l/400th the size of those in creams and lotions prepared without applying high pressure.
  • Microfluidization allows one to prepare elegant stable creams and lotions containing effective amounts of an oxa diacid without the use of traditional emulsifiers and surfactants.
  • the topical compositions of the invention can also be formulated as a micro-emulsion.
  • a first, basic micro-emulsion system comprises about 0.1 to about 50%, preferably from about 1 to about 30%, and most preferably about 5 to about 20% of the oxa diacid, from about 0.5 to about 20% of a hydrocarbon, from about 0.5 to about 20% of an oil, and the remainder water.
  • a second, more preferred micro-emulsion system comprises about 1 to about 20% of the oxa diacid, from about 0.5 to about 15% of a hydrocarbon, from about 1 to about 15% of an oil, from about 0.1 to about 10% of a fatty alcohol, up to 30% of an nonionic surfactant, and the remainder water.
  • compositions of the invention can be formulated as oil-in-water or water-in-oil emulsions, gels, lotions, ointments, sticks, sprays, tapes, patches.
  • inventive compositions can also be in the form of a multiphase emulsion, such as a water-in-oil- in-water type emulsion as disclosed in U.S. Patent No. 4,254,105, incorporated herein by reference.
  • the compositions of the invention can also be formulated as triple emulsions of the oil-in-water-silicone fluid type disclosed in U.S. Patent No. 4,960,764, incorporated herein by reference.
  • compositions of the invention can also be made as a liposomal formulation, for example, according to the methods d scribed in Mezei, J. Pharmaceut. Pharmacol., vol. 34, pp. 473-474 (1982), or modification thereof.
  • droplets of the oxa diacid solution can be entrapped inside the liposomal vesicles with the shell of the liposome being a phospholipid or other suitable lipids (e.g. skin lipids) .
  • the liposomes can then be added to any of the carrier systems described above according, for example, to the preparation modes, uses and compositions of topical liposomes described in Mezei, Topics in Pharmaceutical Sciences, Brei er et al. Eds., pp. 345-358, Elsevier Science Publishers BV, New York (1985), incorporated herein by reference, or according to the reverse-phase evaporation method described in Szoka et al., Proc. Nat. Acad. Sciences, vol. 75, pp. 4194-4198 (1978), and Diploses et al., J. Soc. Cosmetic Chemists, vol.
  • Solutions of oxa diacids can also be entrapped in polymeric vesicles with a shell consisting of a suitable polymeric material such as gelatin, cross-linked gelatin, polyamide, poylacrylates and the like to form a vesicle that is then incorporated into the topical composition.
  • compositions of the invention can include only an oxa compound as an active ingredient, or can use the oxa compound in combinations with other cosmetic and pharmaceutical actives and excipients.
  • Suitable other cosmetic and pharmaceutical agents include, but are not limited to, antifungals, vitamins, sunscreens, retinoids, antiallergenic agents, depigmenting agents, anti-inflammatory agents, anesthetics, surfactants, moisturizers, exfolients, stabilizers, preservatives, antiseptics, thickeners lubricants, humectants, chelating agents and skin penetration enhancers, as well as the emulsifiers, emollients, fragrances and colorants discussed above.
  • thickening agents examples include xanthan gum, xanthan gum brine tolerant, hydroxypropyl cellulose, hydroxyethyl cellulose, carbopol and gum acacia, Sepigel 305 (available from Seppic Co., France), vee-gum or magnesium aluminum silicate.
  • oxa diacids are also compatible with, and their utility can be enhanced by, humectants such as urea, PCA, amino acids, certain polyols and other compounds with hygroscopic properties.
  • Topical compositions can also be formed to contain about about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacid, in combination with a keratolytic agent, such as salicylic acid and benzoyl peroxide, and skin lightening agents such as kojic acid benzoquinone, licorice derivatives, ascorbic acid and its derivatives (e.g. magnesium ascorbyl phosphate), and glycerhetinic acid and its derivatives.
  • a keratolytic agent such as salicylic acid and benzoyl peroxide
  • skin lightening agents such as kojic acid benzoquinone, licorice derivatives, ascorbic acid and its derivatives (e.g. magnesium ascorbyl phosphate), and glycerhetinic acid and its derivatives.
  • organic and inorganic sunscreens such as titanium dioxide, zinc oxide, benzylidene camphor, anthranilates, butylmethoxydibenzoylmethane, naphtholsulphonates and cinnamic acid derivatives
  • organic and inorganic sunscreens such as titanium dioxide, zinc oxide, benzylidene camphor, anthranilates, butylmethoxydibenzoylmethan
  • Topical compositions of the invention can also contain about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacids co-formulated with (i) retinoids such as retinol, retinoic acid, retinyl palmitate, retinyl propionate, retinyl acetate, isotretinoin as well as synthetic retinoid mimics; (ii) hormonal compounds such as estriol, estradiol, estrone or conjugated estrogens; (iii) alpha-hydroxyacids or polyhydroxy alpha-hydroxy acid such as glycolic acid, lactic acid, tartaric acid, gulonic acid and other carboxylic acids and their monomeric, polymeric, cyclic or acyclic derivatives; (iv) alpha-keto acids such as pyruvic acid, 2-oxopropanoic acid, 2-oxobutanoic acid, 2-oxopentanoic acid, and the like.
  • vitamins including, for example, enzyme co- factors such as vitamin B6, vitamin B12, vitamin D3, 1,25-dihydroxy vitamin D3, vitamin Bl, vitamin B2 , vitamin K, vitamins E, tocotrienols and their derivatives, nicotinic acid and its esters, pantothenic acid and it esters, panthenol, folic acid and its derivatives, choline, carnitine and substances without formal vitamin status or "pseudo vitamins” such as vitamin F or cis,cis-linoleic acid, vitamin M or pteroylglutamic acid, vitamins B10 and Bll, sesame seed factor, ter itin, penicin, insectine, hypomycin and mycoine, vitamin L or anthranilic acid, vitamin L2 or adenylthio ethyl-pentose, myoinositol or cis-1,2,3,5- trans-4-6-cyclohexanehexol and its esters
  • anti-mycobacterial agents such as erythromycin, tetracyclin and related compounds, especially doxycyclin and methacyclin, cephalosporins, penicillins, macrolides, peptide compounds such as novobiocin, vancomycin, oleandomycin paromomycin, leucomycine, amphomycin with macrolide molecules, quinolone derivatives and other compounds that interfere with bacterial cell wall synthesis, membrane function, RNA metabolism, purine, pyrimidine and protein synthesis, respiration or phosphorylation;
  • topical analgesics such as lidocaine, benzocaine, butacaine, tetracaine, clove oil and eugenol, of which benzocaine and lidocaine are most preferred;
  • lipidic compounds essential for the skin's barrier function including, for example, ceramides, essential fatty acids and their esters, especially glycerides, ⁇ -hydroxy fatty acids and their esters derived with alkanols through carboxylic hydroxyl or with, other fatty acids at the omega-hydroxyl, the latter type being most preferred, with phospholipids, cholesterol and its esters, such as cholesteryl hemisuccinate and cholesteryl phospate of which cholesterol phospate and essential fatty acids are most preferred, phytosterols, cholestanol and its derivatives.
  • the lipidic compounds can be added to a topical composition either as singular molecular entities or as a complex mixture of lipids derived from either synthetic, animal or plant sources;
  • antiallergenic agents and HI and/or H2,antihistamines such as diphenylhydramine, clomisole, antazoline, thenaldine, phenyltoloxamine citrate, tricyclic antiallergenics such as ketotifene, dithiaden. and 3-thienylsulfide of thiadene, H2- receptor blockers, especially burimamide, metiamide and cimetidien, cromolic acid and its salts;
  • the oxa-diacids can be used with topical anti-inflammatory agents that can reduce inflammation. These anti-inflammatory agents are used at concentrations from about 0.025% to 10%, preferably, 0.5-1%, with the concentration of the anti-inflammatory adjusted upward or downward depending upon the potency 26
  • steroidal anti- inflammatories that can be used with oxa diacids include hydrocortisone, hydroxytriamcilone, alpha- methyl dexamethasone, dexamethasone phosphate, beclamethasone dipropionate, hydrocortisone valerate, hydrocortisone cyclopentylpropionate, prednisolone, and mixtures thereof, with the most preferred being prednisolone and hydrocortisone; and
  • non-steroidal anti-inflammatories can also be employed, such as described in Rainsford,
  • NSAID's including, for example, oxicams (e.g. piroxicam, isoxicam) , fenamic acid derivatives, meclofenamic acid derivatives (e.g.
  • flufenamic acid derivatives such as ibuprofen, naproxen, benoxaprofen, flubiprofen, ketoprofen, suprofen, of which ibuprofen is most preferred; pyrazolidinediones, of which phenylbutazone is most preferred; acetic acid derivatives, such as diclofenac, fenclofenac, indomethacin, sulindac, of which indomethacin is most preferred; salicylic acid derivatives, such as, for example, asprin, disalacid, and benorylate, of which aspirin and disalacid are most preferred.
  • compositions of the invention may also include safe anti-inflammatory products of natural origin shown to possess anti-inflammatory activity such as aloe vera extracts, extracts from genus Rubis (Rubia Cordifolia) , extracts from genus Commiphom (Commiphora Mukul), willow bark, matricarria flowers, arnica flower, comfrey root, fenugreek seed and the like known to those skilled in the art.
  • Topical compositions of the invention can contain from about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacids in combination with antioxidants with phenolic hydroxy functions such as gallic acid derivataives (e.g. propyl gallate) , bio-flavonoids (e.g. quercetin, rutin, daidzein, genistein) , ferrulic acid derivatives (e.g. ethyl ferrulate, sodium ferrulate) , 6-hydroxy-2,5,7,tetra-, methylchroman-2- carboxylic acid.
  • the compositions may also contain effective concentrations of water soluble antioxidants such as uric acid, reductic acid, tannic acid, rosmarinic acid and catechins.
  • the nitric oxide synthase inhibitors can be added at concentrations from about 0.05% to 10%, most preferably from 1% to 3%, and selected from the group including guanidine derivatives, especially monoaminoguianidine and methylguanidine, L-arginine derivatives, especially N *3 - nitro-L-arginine and its esters, N ⁇ -monomethyl-L- arginine, 2-iminopipperidines and other 2- iminoazaheterocycles.
  • guanidine derivatives especially monoaminoguianidine and methylguanidine
  • L-arginine derivatives especially N *3 - nitro-L-arginine and its esters
  • N ⁇ -monomethyl-L- arginine 2-iminopipperidines and other 2- iminoazaheterocycles.
  • compositions may contain those that have one or more thiol functions (-SH) , in either reduced or non-reduced form, such as glutathione, lipoic acid, thioglycolic acid, and other sulfhydryl compounds.
  • thiol functions such as glutathione, lipoic acid, thioglycolic acid, and other sulfhydryl compounds.
  • the levels of sulfhydryl antioxidants should not exceed 0.5% for cosmetic uses of the composition but may be higher for pharmaceutical uses as dictated by the considerations of efficacy.
  • the composition may also include inorganic antioxidants such as sulfites, bisulfites, etabi- sulfite, or other inorganic salts and acids containing sulfur in oxidation state +4.
  • compositions of the invention can also include from about 0.1 to about 90%, preferably from about 1 to about 50%, and most preferably about 5 to about 20% of the oxa diacids coformulated with about 0.025% to 5%, with 0.5%-2% preferred and with 0.5-1% most preferred, of compounds known to be electron spin-traps such as nitrones, N-tertbutyl-nitrone and ⁇ -(4-pyridyl- 1-oxide)-N-tertbutylnitrone or other compounds known to form free radicals with half-life times of more than one minute.
  • compositions that contain insect repellents such as aliphatic, cyclic or aromatic amides, citronella oil, terpineol, cieole, neem oil and terephthalic acid and its esters.
  • insect repellents such as aliphatic, cyclic or aromatic amides, citronella oil, terpineol, cieole, neem oil and terephthalic acid and its esters.
  • suitable insect repellents can be found in Technical Bulletin No. 1549 from the U.S. Department of Agriculture or in their Agricultural Handbook Nos. 69, 340 and 461.
  • the oxa diacid-containing topical compositions of the invention can also contain skin cooling compounds such as, by way of example, menthol, menthyl glycerol, assymetical carbonates, thiocarbonates and urethanes, N-substituted carboxamides, ureas or phosphine oxides such as described in J. Cos et. Chem., vol. 29, p. 185 (1978), menthyl lactate, and menthone glycerine acetal,
  • skin cooling compounds such as, by way of example, menthol, menthyl glycerol, assymetical carbonates, thiocarbonates and urethanes, N-substituted carboxamides, ureas or phosphine oxides such as described in J. Cos et. Chem., vol. 29, p. 185 (1978), menthyl lactate, and menthone glycerine acetal,
  • the general activity and mildness to skin of the present topical compositions can also be enhanced by neutralization to pH 3.5 to 7.0, most preferably from pH 3.7 to 5.6, with one or more amphoteric and pseudoamphoteric compounds such as glycine, alanine, valine, serine, thionine, methionine, leucine, asparagine, histidine, glutamic acid, glutamine, lysine, cystine, cystein, tryptophan, serine, phenylalanine, citrulline, creatine, proline, 3- or 4- hydroxyproline, 5-hydroxylysine, ornithine and its derivatives, 3-aminopropanoic acid and other aminocarboxylic acids, canavanine, canaline, homoarginine, taurine, aminoaldonic acids and aminosugars, aminouronic acid, aminoaldaric acid, deacetylated hyaluronic acid, hyalobiuronic acid, chondrosine, desul
  • chelating agents include those that have a high affinity for zinc, calcium, magnesium, iron and/or copper ions, such as ethylene-diamine-tetra-acetic acid, (ethylenedioxy)- diethylene-dinitrilo-tetra-acetic acid, salicylaldoxime, quinolinol, diaminocyclohexane-tetra- acetic acid, diethylene-triaminopenta-acetic acid, dimethylglyoxime, benzoin oxi e, triethylenetetramine, desferrioxamine or mixtures thereof.
  • the present invention also includes methods by which these compounds can be used to address the aforementioned skin conditions.
  • Such methods include topically applying an effective amount of one or more compound of Formula (I) to the affected skin areas, normally once or twice daily.
  • Such methods also include topically applying a composition containing an effective amount of one or more compounds of Formula (I) in a physiologically acceptable vehicle to the affected skin areas, normally once or twice daily.
  • the methods of the present invention include the topical application of the compounds of Formula (I) in concentrations of up to 100%, when such compounds are a liquid at ambient temperature (e.g. 3, 6, 9-trioxaun- decanedioic acid) , and when using the oxa compounds, for example, for skin peels or for softening hair.
  • the following examples are illustrative of the present invention and are not intended to limit the invention.
  • compositions of the present invention are generally made into lotions, creams or gels for topical application.
  • phase A In a suitable vessel, water, glycerin, propylene glycol Na 2 EDTA and trioxaundecanoic acid are added and mixed together. Ammonium hydroxide is added to the vessel in increments to adjus pH to the desired range. This pH-adjusted phase is then heated to 170-175°F. Hydroxyethyl cellulose is next added with agitation until uniform to complete phase A.
  • phase B is added to a suitable, second vessel, combined and heated to 170- 175°F.
  • Phase B is then added to phase A with sufficient mixing, again at 170-175°F.
  • the batch is then cooled to 120°F.
  • Phase C is added to the batch and mixed until uniform.
  • Phase (A) water glycerin propylene glycol disodium-EDTA
  • the exfoliation patch test procedure involves a 24-hour occlusive patching to a skin site. Skin gradings are conducted immediately, and 24 hours after, removal of the patch. The test focuses primarily on product effects on the stratum corneum and mainly on exfoliation.
  • a corneocyte removing activity sampling (a "CRAS") is taken following the visual grading at 24 hours after removal of the patch.
  • a CRAS score is a quantitative measure of corneocyte desquamation and its calculation is based on the amount of corneocytes removed with each sampling.
  • a series of studies were conducted, the first of which showed that in a 1-day exfoliation CRAS assay, a 10 wt% 3, 6, 9-trioxaundecanedioic acid composition at pH 3.7 had superior exfoliating activity compared to a formulation containing 4 wt% glycolic acid at pH 3.8.
  • This example illustrates a cream that can be prepared and used to reduce appearance of hyper- pigmentation spots on the skin of hands.
  • W/W% isopropyl myristate 3.0 polyethylene glycol (1000) monostearate 5.0 palmitic acid 10.0 3, 6, 9, 12-tetraoxatetradecanedioic acid 10.0 glycerine. 3.0 polyethylene glycol (300) monostearate 5.0 methyl paraben 0.2 magnesium ascorbyl phosphate 2.0 water 60.0 perfume & color to 100.0 triethanolamine to pH 4.0
  • EXAMPLE 4 Cream for Dry Skin, Ichthvosis and Hyperkeratoses This example illustrates a silicone cream that can be prepared and used to treat dry skin, ichthyosis and hyper-keratoses according to the present invention.
  • This example illustrates a water-in-silicone gel composition.
  • EXAMPLE 6 Cream for Acne, Skin Blemishes and Age Spots This example illustrates a face cream than can be used to treat acne, skin blemishes and age spots. W/ %
  • Phase A oleic acid 1.0 stearic acid 17.0 polyoxyethylene (20 propylene glycol onostrearate) 10.0 retinol 0.1 Phase B glycerine

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Abstract

L'invention porte sur l'utilisation des composés définis par la formule (I) en tant que principes actifs pour traiter des problèmes cutanés, sur des compositions contenant ces composés et sur des méthodes de traitement de problèmes cutanés, au moyen de ces composés et de ces compositions. Dans la formule (I), R4 est (CR5R6-CR7R8-X1)n-CR9R10-C(=X2)X3R11, n est un nombre entier entre 1 et 18; R1, R2, R3, R5, R6, R7, R8, R9, R10 et R11, sont indépendamment des substituants hydrogène ou non-hydrogène; et X, X1, X2, X3, Y et Z sont indépendamment 0, NH, ou S.
PCT/US1997/006973 1996-04-25 1997-04-25 Diacide oxa et composes voisins pour traiter les problemes de peau WO1997039726A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP53835597A JP3779733B2 (ja) 1996-04-25 1997-04-25 皮膚の状態処置用のオキサ二酸および関連化合物
BR9708747-5A BR9708747A (pt) 1996-04-25 1997-04-25 Oxa diácidos e compostos relacionados para o tratamento de condições da pele
EP97924518A EP0910331B1 (fr) 1996-04-25 1997-04-25 Oxadiacides et composes voisins pour traiter les problemes de peau
CA2251746A CA2251746C (fr) 1996-04-25 1997-04-25 Diacide oxa et composes voisins pour traiter les problemes de peau
DE69730604T DE69730604T2 (de) 1996-04-25 1997-04-25 Oxadisäuren und verwandte verbindungen zur behandlung von hautstörungen
AT97924518T ATE275383T1 (de) 1996-04-25 1997-04-25 Oxadisäuren und verwandte verbindungen zur behandlung von hautstörungen

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US08/636,540 US5834513A (en) 1996-04-25 1996-04-25 Oxa diacids and related compounds for treating skin conditions
US08/636,540 1996-04-25

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EP (1) EP0910331B1 (fr)
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AR (1) AR006867A1 (fr)
AT (1) ATE275383T1 (fr)
BR (1) BR9708747A (fr)
CA (1) CA2251746C (fr)
DE (1) DE69730604T2 (fr)
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CA2251746A1 (fr) 1997-10-30
CN1216460A (zh) 1999-05-12
JP2000510456A (ja) 2000-08-15
EP0910331A1 (fr) 1999-04-28
AR006867A1 (es) 1999-09-29
CA2251746C (fr) 2011-04-19
ATE275383T1 (de) 2004-09-15
US5834513A (en) 1998-11-10
DE69730604T2 (de) 2005-09-29
EP0910331B1 (fr) 2004-09-08
EP0910331A4 (fr) 1999-11-03
BR9708747A (pt) 2000-01-04
DE69730604D1 (de) 2004-10-14
CN1139375C (zh) 2004-02-25
JP3779733B2 (ja) 2006-05-31

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